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Luxury Greek Island holidays

Picture the quintessential Greek holiday scene: small white pebble coves and soft sandy beaches; friendly harbourside tavernas and silvery olive groves; tiny hamlets, historic towns and peaceful churches. Our carefully chosen Greek Island destinations and handpicked collection of luxury villas and boutique hotels offer all this and more. 

Often described as stepping back in time, the Greek Islands offer a heady combination of ancient landscapes, stunning coastlines and picturesque fishing villages. And yet within this mix of fascinating history and rich culture, a Simpson Travel luxury villa or hotel holiday allows you to experience the Mediterranean at your own pace, which can be as slow as you want it to be.

Which Greek Island is for you?

While the blue seas, stunning views and pine-scented countryside are part of all our Greek Island destinations, there are distinguishing features that give each island its own identity.

Explore the UNESCO-listed Corfu Town or ancient ruins of Knossos in Crete; tap into the exclusive tranquillity of Meganissi or the simplicity of a beach holiday on diminutive Paxos – whichever you choose, there’s a unique Greek Island holiday waiting to happen. You may prefer Skopelos and Kefalonia as featured in the movies, or the Homeric history of Ithaca, but for a family holiday with young children, our crèches and children’s clubs on Lefkada and Zakynthos tick many boxes. After all, with professional nannies on standby, mummies and daddies can have some well-earned time out.

Things to do on the Greek Islands

When you want to venture further afield than your own private villa swimming pool or the peaceful garden of your boutique hotel, you’ll be spoiled for choice. Hire a boat and find a secluded bay far away from the modern world. Explore the winding streets of pretty villages or go walking through pine forests and ancient olive groves. A Greek Island holiday with Simpson Travel allows you to experience the authentic Mediterranean – and that includes the food: freshly caught fish, hearty meat dishes and shining Greek salads that can be consumed leisurely with a carafe of wine at a table overlooking the sea.

This is your Greek Island holiday – so what will it be?

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Cedar Bay Beachside Villas – Ammos

Chania & West Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Beautiful beachside villa in SW Crete
  • Adult only
  • Stylish and contemporary
  • Taverna 5-minute walk

Prices are based on 2 sharing for 7 nights on Tuesday 6 April 2021

Package holiday

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$1,287pp Total price $2,574
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Cedar Bay Beachside Villas – Kedros

Chania & West Crete, Crete, Greece

Villa | Bedroom 1 | Sleeps 2

  • Beautiful beachside villa in SW Crete
  • Adult only
  • Stylish and contemporary
  • Taverna 5-minute walk

Prices are based on 2 sharing for 7 nights on Tuesday 6 April 2021

Package holiday

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  • Return flights from London Gatwick Airport
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$1,287pp Total price $2,574
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Simpson Kids

Whether you're travelling with babes in arms, toddlers or school-age children, our Simpson Kids programme will help you find the perfect holiday to suit your family. From hotels with expert childcare to villas with complimentary infant packs and garden games for the kids, we have everything you need for a stress-free family holiday.
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Acqua di Mare – Villa Siena

Lefkada, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Stunning beach front location
  • Stylish and contemporary
  • Lawned garden
  • Simpson family extras available

Prices are based on 2 sharing for 7 nights

Package holiday

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  • Departs 02 May 2021

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$1,321pp Total price $2,642
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  • Departs 10 Oct 2021

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Villa Kambos

Palekastro & Far East Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Short walk to best beach in Crete
  • Set in unspoilt Xerokambos
  • Beautiful views
  • Short drive to tavernas

Prices are based on 2 sharing for 7 nights

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  • Departs 11 May 2021

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$1,330pp Total price $2,659
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  • Departs 19 Oct 2021

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The Bay House

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Light and airy house
  • Beautiful views of Vathy
  • Comfortable and welcoming
  • Vathy shops and restaurants 5min drive

Prices are based on 2 sharing for 7 nights on Saturday 1 May 2021

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$1,351pp Total price $2,702
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Cedar Bay Beachside Villas – Lithos

Chania & West Crete, Crete, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Beautiful beachside villa in SW Crete
  • Adult only
  • Stylish and contemporary
  • Taverna 5-minute walk

Prices are based on 2 sharing for 7 nights on Tuesday 6 April 2021

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  • Return flights from London Gatwick Airport
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$1,355pp Total price $2,710
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Villa Santolina

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish contemporary villa
  • Beautiful views
  • Walking distance to sandy beach and tavernas
  • Simpson family extras

Prices are based on 2 sharing for 7 nights on Sunday 2 May 2021

Package holiday

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$1,363pp Total price $2,726
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Villa Melia

Lefkada, Greece

Villa | Bedrooms 3 | Sleeps 6

  • Stylish sea front villa
  • Beautiful sea views
  • Steps down to private pontoon
  • Walking distance to tavernas

Prices are based on 2 sharing for 7 nights on Sunday 2 May 2021

Package holiday

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  • Return flights from London Gatwick Airport
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$1,363pp Total price $2,726
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The Harbour House

Paxos, Greece

Villa | Bedroom 1 | Sleeps 2

  • Delightful harbour house suite
  • Gaios waterfront
  • Roof terrace with harbour views
  • Shops and restaurants on your doorstep

Prices are based on 2 sharing for 7 nights on Wednesday 6 October 2021

Package holiday

  • Suite
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$1,384pp Total price $2,768
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Neritos House

Ithaca, Greece

Villa | Bedrooms 2 | Sleeps 4

  • Comfortable welcoming house
  • Stunning sea and mountain views
  • Light and airy
  • Vathy shops and restaurants 5min drive

Prices are based on 2 sharing for 7 nights on Saturday 1 May 2021

Package holiday

  • Villa
  • Return flights from London Gatwick Airport
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Prices
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$1,391pp Total price $2,781
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Reviews

Simpson Travel in the press

  • ‘[Simpson Travel] specialise in the sort of magical, unspoilt destinations my family loves’ Author: The Telegraph

  • ‘So how did we find the near-perfection that was Villa Cabanellas in Mallorca? The first step was to approach… Simpson Travel… we needed expertise, not just blinding choice.’ Author: Sunday Times Travel Magazine, The Villas Handbook

  • ‘The Simpson Travel check-in at Heathrow’s Terminal 5 was seamless.’ Author: Family Traveller, Katy Hill

  • ‘Where Simpson [Exclusive] really excels is in its first-hand knowledge of properties and destinations’ Author: House & Garden

  • ‘Simpson [Exclusive] delivers holidays that combine sunshine, five-star luxury and friendly service’ Author: House & Garden

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Holiday ideas

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Travel advice from the Foreign Office

For up-to-date advice and information on travelling abroad, including passports, visas and health and safety, please visit the Foreign Commonwealth & Development Office website or call 020 7008 1500.

The air holidays and flights shown are ATOL protected by the Civil Aviation Authority. Our ATOL number is ATOL 5858. ATOL protection extends primarily to customers who book and pay in the United Kingdom. Find out more about ATOL. Simpson Travel is the trading name of Far & Wide Ltd.

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